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Chemodex
N-Dodecanoyl-L-homoserine lactone
Product Details | |
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Synonyms | N-[(3S)-Tetrahydro-2-oxo-3-furanyl]-dodecanamide; dDHL; C12-HSL |
Product Type | Chemical |
Properties | |
Formula | C16H29NO3 |
MW | 283.4 |
CAS | 137173-46-7 |
Source/Host Chemicals | Synthetic. |
Purity Chemicals | ≥98% (NMR) |
Appearance | White powder. |
Solubility | Soluble in DMSO and dimethylformamide (approx. 30mg/ml). |
Identity | Determined by 1H-NMR. |
Declaration | Manufactured by Chemodex. |
Other Product Data |
Click here for Original Manufacturer Product Datasheet |
InChi Key | WILLZMOKUUPJSL-AWEZNQCLSA-N |
Smiles | CCCCCCCCCCCC(=O)N[C@H]1CCOC1=O |
Shipping and Handling | |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | +4°C |
Handling Advice |
Keep cool and dry. Protect from light and moisture. |
Use/Stability | Stable for at least 2 years after receipt when stored at +4°C. |
Documents | |
MSDS | Inquire |
Product Specification Sheet | |
Datasheet | Download PDF |
N-Dodecanoyl-L-homoserine lactone (C12-HSL) is a small diffusible signalling molecule involved in quorum sensing, thereby controlling gene expression and affecting cellular metabolism in bacteria. In addition to regulating bacterial functions, C12-HSL activates NF-κB in RAW 264.7 macrophages, increasing the expression of TNF-α, interleukin-1β (IL-1β) and IL-8, while other lactones do not. In addition, C12-HSL alters cell cycling and metabolism of human keratinocyte (HaCaT) cells. It is important to note that C12-HSL is distinct from N-3-oxo-dodecanoyl-L-homoserine lactone, which is produced at different times in biofilm development and has different cellular effects.
(1) G.D. Geske; JACS 127, 12762 (2005) | (2) J.T. Hodgkinson; Tetrahedron Lett. 52, 3291 (2011) | (3) A. Kuo, et al.; J. Bacteriol. 176, 7558 (1994) | (4) J.K. Lithgow, et al.; Mol. Microbiol. 37, 81 (2000) | (5) K.H. McClean, et al.; Microbiol. 143, 3703 (1997) | (6) K. Gomi, et al.; Infect. Immun. 74, 7029 (2006) | (7) S. Kristiansen, et al.; APMIS 116, 361 (2008) | (8) Y. Huang, et al.; ISME 1, (2008)